Page last updated: 2024-12-08

1-(4-methoxyphenyl)piperazine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

1-(4-Methoxyphenyl)piperazine, also known as **mCPP**, is a **pharmacological research tool** that acts as a **serotonin agonist**. It is not a drug for human consumption and is primarily used in laboratory settings to study serotonin function and its role in various physiological and psychological processes.

**Here's why it is important for research:**

* **Selective serotonin agonist:** mCPP acts predominantly on serotonin receptors, particularly the 5-HT2C receptor, which is known to be involved in mood regulation, appetite control, and other brain functions. This selectivity allows researchers to isolate the effects of serotonin activation.
* **Wide range of effects:** mCPP can induce various physiological and psychological responses, including:
* **Hallucinations:** It can trigger visual, auditory, and tactile hallucinations.
* **Mood changes:** It can elicit both positive and negative mood alterations, including anxiety, depression, and euphoria.
* **Cognitive effects:** It can impact attention, memory, and decision-making.
* **Physiological changes:** It can affect body temperature, blood pressure, and heart rate.
* **Understanding serotonin's role:** By studying the effects of mCPP, researchers can gain insights into the complex role of serotonin in the brain and its implications for conditions like:
* **Depression and anxiety disorders:** Understanding the effects of serotonin on mood and cognition can help develop new therapies for these conditions.
* **Schizophrenia and other psychotic disorders:** mCPP's ability to induce hallucinations helps researchers study the underlying mechanisms of psychosis.
* **Obesity and eating disorders:** Investigating serotonin's role in appetite control could lead to novel approaches for treating these conditions.
* **Drug development:** mCPP has been used to screen for new drugs that target serotonin receptors, potentially leading to the development of more effective and safer medications.

**Important Note:** mCPP is a potent compound with potentially dangerous side effects. It is **not safe for human consumption** and should only be used under strict laboratory conditions by qualified researchers.

1-(4-methoxyphenyl)piperazine: a designer drug; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID269722
CHEMBL ID59517
SCHEMBL ID234280
MeSH IDM0472801

Synonyms (52)

Synonym
AC-573
unii-p385m92gyg
einecs 253-829-7
n-(p-methoxyphenyl)piperazine
p385m92gyg ,
OPREA1_137034
OPREA1_331497
1-(4-methoxyphenyl)piperazine, 97%
1-(4-methoxyphenyl)piperazine
STK397317
38212-30-5
AKOS000101163
CHEMBL59517 ,
bdbm50001913
1-(4-methoxy-phenyl)-piperazine
4-methoxyphenylpiperazine
A6487
n-(4-methoxyphenyl)piperazine
FT-0605865
LF-0567
SCHEMBL234280
4-methoxy phenylpiperazine
4-methoxyphenypiperazine
1-(4-metoxyphenyl)-piperazine
4-(4-methoxyphenyl)piperazine
1-(4-methoxyphenyl)-piperazine
4-(piperazin-1-yl)anisole
4 -(4-methoxyphenyl)piperazine
4-methoxyphenyl piperazine
n-(4-methoxyphenyl)-piperazine
piperazine, 1-(4-methoxyphenyl)-
4-meopp
AE-641/00358012
W-106495
1-(4-methoxyphenyl-piperazine)
4-mpp
1-(p-anisyl)piperazine
paraperazine
para-methoxyphenylpiperazine
mfcd00040736
meopp
J231.894F ,
n-(4-methoxyphenyl)pperazne
J-523067
F2190-0350
DTXSID30191591
n-(p-methoxyphenyl)piperazine (pmeopp)
Q7133617
posaconazole impurity mppa
AMY33096
SY002316
PD047414

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" The aim of this work was to evaluate the toxic effects of BZP, MeOPP and MDBP using Caenorhabditis elegans as in vivo model for acute toxicity, development, reproduction and behavior testing."( Piperazine designer drugs elicit toxicity in the alternative in vivo model Caenorhabditis elegans.
Arbo, MD; Ávila, DS; Bastos, ML; Carmo, H; Cestonaro, LV; Eifler-Lima, V; Garcia, I; Garcia, SC; Göethel, G; Peruzzi, CP; Souto, C, 2020
)
0.56
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (7)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 3EHomo sapiens (human)Ki1.64000.00100.88359.9000AID6343
5-hydroxytryptamine receptor 3BHomo sapiens (human)Ki1.64000.00100.87119.9000AID6343
Beta-1 adrenergic receptorHomo sapiens (human)IC50 (µMol)38.00000.00021.46819.0000AID42027
5-hydroxytryptamine receptor 3AHomo sapiens (human)Ki1.64000.00000.74119.9000AID6343
Beta-2 adrenergic receptorCanis lupus familiaris (dog)IC50 (µMol)100.00000.00012.45965.2000AID40701
5-hydroxytryptamine receptor 3DHomo sapiens (human)Ki1.64000.00100.88359.9000AID6343
5-hydroxytryptamine receptor 3CHomo sapiens (human)Ki1.64000.00100.88359.9000AID6343
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (26)

Processvia Protein(s)Taxonomy
serotonin receptor signaling pathway5-hydroxytryptamine receptor 3EHomo sapiens (human)
monoatomic ion transmembrane transport5-hydroxytryptamine receptor 3EHomo sapiens (human)
excitatory postsynaptic potential5-hydroxytryptamine receptor 3EHomo sapiens (human)
inorganic cation transmembrane transport5-hydroxytryptamine receptor 3EHomo sapiens (human)
regulation of membrane potential5-hydroxytryptamine receptor 3EHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 3EHomo sapiens (human)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 3BHomo sapiens (human)
monoatomic ion transmembrane transport5-hydroxytryptamine receptor 3BHomo sapiens (human)
excitatory postsynaptic potential5-hydroxytryptamine receptor 3BHomo sapiens (human)
inorganic cation transmembrane transport5-hydroxytryptamine receptor 3BHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 3BHomo sapiens (human)
regulation of membrane potential5-hydroxytryptamine receptor 3BHomo sapiens (human)
positive regulation of heart rate by epinephrine-norepinephrineBeta-1 adrenergic receptorHomo sapiens (human)
positive regulation of the force of heart contraction by epinephrine-norepinephrineBeta-1 adrenergic receptorHomo sapiens (human)
diet induced thermogenesisBeta-1 adrenergic receptorHomo sapiens (human)
response to coldBeta-1 adrenergic receptorHomo sapiens (human)
heat generationBeta-1 adrenergic receptorHomo sapiens (human)
negative regulation of multicellular organism growthBeta-1 adrenergic receptorHomo sapiens (human)
fear responseBeta-1 adrenergic receptorHomo sapiens (human)
regulation of circadian sleep/wake cycle, sleepBeta-1 adrenergic receptorHomo sapiens (human)
brown fat cell differentiationBeta-1 adrenergic receptorHomo sapiens (human)
regulation of postsynaptic membrane potentialBeta-1 adrenergic receptorHomo sapiens (human)
adenylate cyclase-activating adrenergic receptor signaling pathwayBeta-1 adrenergic receptorHomo sapiens (human)
positive regulation of cold-induced thermogenesisBeta-1 adrenergic receptorHomo sapiens (human)
norepinephrine-epinephrine-mediated vasodilation involved in regulation of systemic arterial blood pressureBeta-1 adrenergic receptorHomo sapiens (human)
positive regulation of MAPK cascadeBeta-1 adrenergic receptorHomo sapiens (human)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 3AHomo sapiens (human)
monoatomic ion transmembrane transport5-hydroxytryptamine receptor 3AHomo sapiens (human)
excitatory postsynaptic potential5-hydroxytryptamine receptor 3AHomo sapiens (human)
inorganic cation transmembrane transport5-hydroxytryptamine receptor 3AHomo sapiens (human)
regulation of presynaptic membrane potential5-hydroxytryptamine receptor 3AHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 3AHomo sapiens (human)
regulation of membrane potential5-hydroxytryptamine receptor 3AHomo sapiens (human)
receptor-mediated endocytosisBeta-2 adrenergic receptorCanis lupus familiaris (dog)
regulation of smooth muscle contractionBeta-2 adrenergic receptorCanis lupus familiaris (dog)
positive regulation of MAPK cascadeBeta-2 adrenergic receptorCanis lupus familiaris (dog)
negative regulation of G protein-coupled receptor signaling pathwayBeta-2 adrenergic receptorCanis lupus familiaris (dog)
adenylate cyclase-activating adrenergic receptor signaling pathwayBeta-2 adrenergic receptorCanis lupus familiaris (dog)
positive regulation of autophagosome maturationBeta-2 adrenergic receptorCanis lupus familiaris (dog)
positive regulation of lipophagyBeta-2 adrenergic receptorCanis lupus familiaris (dog)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 3DHomo sapiens (human)
monoatomic ion transmembrane transport5-hydroxytryptamine receptor 3DHomo sapiens (human)
excitatory postsynaptic potential5-hydroxytryptamine receptor 3DHomo sapiens (human)
inorganic cation transmembrane transport5-hydroxytryptamine receptor 3DHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 3DHomo sapiens (human)
regulation of membrane potential5-hydroxytryptamine receptor 3DHomo sapiens (human)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 3CHomo sapiens (human)
monoatomic ion transmembrane transport5-hydroxytryptamine receptor 3CHomo sapiens (human)
excitatory postsynaptic potential5-hydroxytryptamine receptor 3CHomo sapiens (human)
inorganic cation transmembrane transport5-hydroxytryptamine receptor 3CHomo sapiens (human)
regulation of membrane potential5-hydroxytryptamine receptor 3CHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 3CHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
serotonin-gated monoatomic cation channel activity5-hydroxytryptamine receptor 3EHomo sapiens (human)
excitatory extracellular ligand-gated monoatomic ion channel activity5-hydroxytryptamine receptor 3EHomo sapiens (human)
transmitter-gated monoatomic ion channel activity involved in regulation of postsynaptic membrane potential5-hydroxytryptamine receptor 3EHomo sapiens (human)
serotonin-gated monoatomic cation channel activity5-hydroxytryptamine receptor 3BHomo sapiens (human)
transmitter-gated monoatomic ion channel activity involved in regulation of postsynaptic membrane potential5-hydroxytryptamine receptor 3BHomo sapiens (human)
excitatory extracellular ligand-gated monoatomic ion channel activity5-hydroxytryptamine receptor 3BHomo sapiens (human)
beta-adrenergic receptor activityBeta-1 adrenergic receptorHomo sapiens (human)
beta1-adrenergic receptor activityBeta-1 adrenergic receptorHomo sapiens (human)
protein bindingBeta-1 adrenergic receptorHomo sapiens (human)
PDZ domain bindingBeta-1 adrenergic receptorHomo sapiens (human)
alpha-2A adrenergic receptor bindingBeta-1 adrenergic receptorHomo sapiens (human)
protein heterodimerization activityBeta-1 adrenergic receptorHomo sapiens (human)
G protein-coupled neurotransmitter receptor activity involved in regulation of postsynaptic membrane potentialBeta-1 adrenergic receptorHomo sapiens (human)
protein binding5-hydroxytryptamine receptor 3AHomo sapiens (human)
serotonin-gated monoatomic cation channel activity5-hydroxytryptamine receptor 3AHomo sapiens (human)
identical protein binding5-hydroxytryptamine receptor 3AHomo sapiens (human)
serotonin binding5-hydroxytryptamine receptor 3AHomo sapiens (human)
ligand-gated monoatomic ion channel activity involved in regulation of presynaptic membrane potential5-hydroxytryptamine receptor 3AHomo sapiens (human)
transmitter-gated monoatomic ion channel activity involved in regulation of postsynaptic membrane potential5-hydroxytryptamine receptor 3AHomo sapiens (human)
excitatory extracellular ligand-gated monoatomic ion channel activity5-hydroxytryptamine receptor 3AHomo sapiens (human)
beta2-adrenergic receptor activityBeta-2 adrenergic receptorCanis lupus familiaris (dog)
protein homodimerization activityBeta-2 adrenergic receptorCanis lupus familiaris (dog)
norepinephrine bindingBeta-2 adrenergic receptorCanis lupus familiaris (dog)
protein binding5-hydroxytryptamine receptor 3DHomo sapiens (human)
serotonin-gated monoatomic cation channel activity5-hydroxytryptamine receptor 3DHomo sapiens (human)
excitatory extracellular ligand-gated monoatomic ion channel activity5-hydroxytryptamine receptor 3DHomo sapiens (human)
transmitter-gated monoatomic ion channel activity involved in regulation of postsynaptic membrane potential5-hydroxytryptamine receptor 3DHomo sapiens (human)
protein binding5-hydroxytryptamine receptor 3CHomo sapiens (human)
serotonin-gated monoatomic cation channel activity5-hydroxytryptamine receptor 3CHomo sapiens (human)
excitatory extracellular ligand-gated monoatomic ion channel activity5-hydroxytryptamine receptor 3CHomo sapiens (human)
transmitter-gated monoatomic ion channel activity involved in regulation of postsynaptic membrane potential5-hydroxytryptamine receptor 3CHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
plasma membrane5-hydroxytryptamine receptor 3EHomo sapiens (human)
postsynaptic membrane5-hydroxytryptamine receptor 3EHomo sapiens (human)
serotonin-activated cation-selective channel complex5-hydroxytryptamine receptor 3EHomo sapiens (human)
neuron projection5-hydroxytryptamine receptor 3EHomo sapiens (human)
transmembrane transporter complex5-hydroxytryptamine receptor 3EHomo sapiens (human)
synapse5-hydroxytryptamine receptor 3EHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 3EHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 3BHomo sapiens (human)
postsynaptic membrane5-hydroxytryptamine receptor 3BHomo sapiens (human)
serotonin-activated cation-selective channel complex5-hydroxytryptamine receptor 3BHomo sapiens (human)
cell surface5-hydroxytryptamine receptor 3BHomo sapiens (human)
transmembrane transporter complex5-hydroxytryptamine receptor 3BHomo sapiens (human)
synapse5-hydroxytryptamine receptor 3BHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 3BHomo sapiens (human)
neuron projection5-hydroxytryptamine receptor 3BHomo sapiens (human)
early endosomeBeta-1 adrenergic receptorHomo sapiens (human)
plasma membraneBeta-1 adrenergic receptorHomo sapiens (human)
Schaffer collateral - CA1 synapseBeta-1 adrenergic receptorHomo sapiens (human)
neuronal dense core vesicleBeta-1 adrenergic receptorHomo sapiens (human)
plasma membraneBeta-1 adrenergic receptorHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 3AHomo sapiens (human)
cleavage furrow5-hydroxytryptamine receptor 3AHomo sapiens (human)
postsynaptic membrane5-hydroxytryptamine receptor 3AHomo sapiens (human)
serotonin-activated cation-selective channel complex5-hydroxytryptamine receptor 3AHomo sapiens (human)
synapse5-hydroxytryptamine receptor 3AHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 3AHomo sapiens (human)
transmembrane transporter complex5-hydroxytryptamine receptor 3AHomo sapiens (human)
neuron projection5-hydroxytryptamine receptor 3AHomo sapiens (human)
early endosomeBeta-2 adrenergic receptorCanis lupus familiaris (dog)
Golgi apparatusBeta-2 adrenergic receptorCanis lupus familiaris (dog)
receptor complexBeta-2 adrenergic receptorCanis lupus familiaris (dog)
plasma membrane5-hydroxytryptamine receptor 3DHomo sapiens (human)
postsynaptic membrane5-hydroxytryptamine receptor 3DHomo sapiens (human)
serotonin-activated cation-selective channel complex5-hydroxytryptamine receptor 3DHomo sapiens (human)
synapse5-hydroxytryptamine receptor 3DHomo sapiens (human)
transmembrane transporter complex5-hydroxytryptamine receptor 3DHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 3DHomo sapiens (human)
neuron projection5-hydroxytryptamine receptor 3DHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 3CHomo sapiens (human)
postsynaptic membrane5-hydroxytryptamine receptor 3CHomo sapiens (human)
serotonin-activated cation-selective channel complex5-hydroxytryptamine receptor 3CHomo sapiens (human)
synapse5-hydroxytryptamine receptor 3CHomo sapiens (human)
transmembrane transporter complex5-hydroxytryptamine receptor 3CHomo sapiens (human)
neuron projection5-hydroxytryptamine receptor 3CHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 3CHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID204444Binding affinity towards sigma receptor in guinea pig brain membranes using [3H]DTG as radioligand1991Journal of medicinal chemistry, Dec, Volume: 34, Issue:12
Novel 1-phenylpiperazine and 4-phenylpiperidine derivatives as high-affinity sigma ligands.
AID6343Compound was tested for the inhibition of [3H]GR-65630 binding to 5-hydroxytryptamine 3 receptor expressed in NG 108-15 cells1996Journal of medicinal chemistry, Sep-27, Volume: 39, Issue:20
Structure-activity relationships for the binding of arylpiperazines and arylbiguanides at 5-HT3 serotonin receptors.
AID40701Binding affinity towards Beta-2 adrenergic receptor by displacing [3H]dihydroalprenolol, in partially purified membrane fractions from canine lung tissue in the presence of 0.1 uM metoprolol1992Journal of medicinal chemistry, Feb-21, Volume: 35, Issue:4
Synthesis, cardiac electrophysiology, and beta-blocking activity of novel arylpiperazines with potential as class II/III antiarrhythmic agents.
AID4091Displacement of [3H]2-(di-N-propylamino)-8-hydroxytetralin from central 5-hydroxytryptamine 1A receptor recognition sites in rat frontal cortex homogenates.1995Journal of medicinal chemistry, May-26, Volume: 38, Issue:11
N4-unsubstituted N1-arylpiperazines as high-affinity 5-HT1A receptor ligands.
AID42027Binding affinity for Beta-1 adrenergic receptor by displacing [3H]dihydroalprenolol, in partially purified membrane fractions from canine ventricular muscle in the presence of 1 uM zinterol1992Journal of medicinal chemistry, Feb-21, Volume: 35, Issue:4
Synthesis, cardiac electrophysiology, and beta-blocking activity of novel arylpiperazines with potential as class II/III antiarrhythmic agents.
AID493017Wombat Data for BeliefDocking1991Journal of medicinal chemistry, Dec, Volume: 34, Issue:12
Novel 1-phenylpiperazine and 4-phenylpiperidine derivatives as high-affinity sigma ligands.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (44.44)18.2507
2000's2 (22.22)29.6817
2010's1 (11.11)24.3611
2020's2 (22.22)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.09

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index28.09 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index25.99 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.09)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]